CA2608977C - Antifungal agents - Google Patents
Antifungal agents Download PDFInfo
- Publication number
- CA2608977C CA2608977C CA2608977A CA2608977A CA2608977C CA 2608977 C CA2608977 C CA 2608977C CA 2608977 A CA2608977 A CA 2608977A CA 2608977 A CA2608977 A CA 2608977A CA 2608977 C CA2608977 C CA 2608977C
- Authority
- CA
- Canada
- Prior art keywords
- phenyl
- oxo
- indolizin
- acetamide
- pyridin
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Active
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- 229940121375 antifungal agent Drugs 0.000 title abstract description 10
- 239000003429 antifungal agent Substances 0.000 title abstract description 7
- 150000001875 compounds Chemical class 0.000 claims abstract description 162
- 150000003839 salts Chemical class 0.000 claims abstract description 53
- 239000000417 fungicide Substances 0.000 claims abstract description 5
- 229910052739 hydrogen Inorganic materials 0.000 claims description 117
- 239000001257 hydrogen Substances 0.000 claims description 117
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 101
- 229910052736 halogen Inorganic materials 0.000 claims description 98
- 150000002367 halogens Chemical class 0.000 claims description 98
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 94
- 125000000623 heterocyclic group Chemical group 0.000 claims description 86
- 125000001424 substituent group Chemical group 0.000 claims description 74
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 72
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 67
- 239000000203 mixture Substances 0.000 claims description 66
- 150000002431 hydrogen Chemical class 0.000 claims description 49
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 48
- -1 -NR'R" Chemical group 0.000 claims description 43
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 39
- 125000004076 pyridyl group Chemical group 0.000 claims description 36
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 31
- 125000004648 C2-C8 alkenyl group Chemical group 0.000 claims description 31
- 125000004649 C2-C8 alkynyl group Chemical group 0.000 claims description 31
- 125000001544 thienyl group Chemical group 0.000 claims description 30
- 125000006656 (C2-C4) alkenyl group Chemical group 0.000 claims description 29
- 125000002541 furyl group Chemical group 0.000 claims description 28
- 208000031888 Mycoses Diseases 0.000 claims description 26
- 125000002947 alkylene group Chemical group 0.000 claims description 26
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 25
- 125000003118 aryl group Chemical group 0.000 claims description 22
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 21
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims description 20
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 20
- 125000003406 indolizinyl group Chemical group C=1(C=CN2C=CC=CC12)* 0.000 claims description 20
- 241000228212 Aspergillus Species 0.000 claims description 17
- 125000005842 heteroatom Chemical group 0.000 claims description 17
- 239000003814 drug Substances 0.000 claims description 15
- 230000002265 prevention Effects 0.000 claims description 15
- 125000000041 C6-C10 aryl group Chemical group 0.000 claims description 14
- 201000010099 disease Diseases 0.000 claims description 14
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 claims description 14
- 238000000034 method Methods 0.000 claims description 14
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 14
- 125000001070 dihydroindolyl group Chemical group N1(CCC2=CC=CC=C12)* 0.000 claims description 13
- 229910052757 nitrogen Inorganic materials 0.000 claims description 13
- 241000222120 Candida <Saccharomycetales> Species 0.000 claims description 12
- 125000004450 alkenylene group Chemical group 0.000 claims description 11
- 125000003386 piperidinyl group Chemical group 0.000 claims description 11
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 10
- 125000003785 benzimidazolyl group Chemical group N1=C(NC2=C1C=CC=C2)* 0.000 claims description 10
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 10
- 125000001041 indolyl group Chemical group 0.000 claims description 10
- 125000003725 azepanyl group Chemical group 0.000 claims description 8
- 125000002757 morpholinyl group Chemical group 0.000 claims description 8
- 239000008194 pharmaceutical composition Substances 0.000 claims description 8
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 7
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 7
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 claims description 6
- 239000005711 Benzoic acid Substances 0.000 claims description 6
- QOSMNYMQXIVWKY-UHFFFAOYSA-N Propyl levulinate Chemical compound CCCOC(=O)CCC(C)=O QOSMNYMQXIVWKY-UHFFFAOYSA-N 0.000 claims description 6
- 125000001664 diethylamino group Chemical group [H]C([H])([H])C([H])([H])N(*)C([H])([H])C([H])([H])[H] 0.000 claims description 6
- 229910052717 sulfur Inorganic materials 0.000 claims description 6
- 125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 claims description 5
- 125000000304 alkynyl group Chemical group 0.000 claims description 5
- 125000004419 alkynylene group Chemical group 0.000 claims description 5
- 229910052799 carbon Inorganic materials 0.000 claims description 5
- 239000003085 diluting agent Substances 0.000 claims description 5
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 5
- 230000002538 fungal effect Effects 0.000 claims description 5
- 125000003342 alkenyl group Chemical group 0.000 claims description 4
- 125000004494 ethyl ester group Chemical group 0.000 claims description 4
- 230000000855 fungicidal effect Effects 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 4
- DKZOGGUIXMEZBI-UHFFFAOYSA-N n-benzyl-2-oxo-2-(2-phenylindolizin-3-yl)acetamide Chemical compound C=1C=CC=CC=1C=1C=C2C=CC=CN2C=1C(=O)C(=O)NCC1=CC=CC=C1 DKZOGGUIXMEZBI-UHFFFAOYSA-N 0.000 claims description 4
- CCPXKHHOEGGLHV-UHFFFAOYSA-N 2-(2-methylindolizin-3-yl)-2-oxoacetic acid Chemical compound C1=CC=CN2C(C(=O)C(O)=O)=C(C)C=C21 CCPXKHHOEGGLHV-UHFFFAOYSA-N 0.000 claims description 3
- 125000000732 arylene group Chemical group 0.000 claims description 3
- 239000003937 drug carrier Substances 0.000 claims description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 3
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 3
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 3
- RFHKDZOMTCGDEG-UHFFFAOYSA-N 2-oxo-n-(2-phenylethyl)-2-(2-phenylindolizin-3-yl)acetamide Chemical compound C=1C=CC=CC=1C=1C=C2C=CC=CN2C=1C(=O)C(=O)NCCC1=CC=CC=C1 RFHKDZOMTCGDEG-UHFFFAOYSA-N 0.000 claims description 2
- JAHIPDTWWVYVRV-UHFFFAOYSA-N 4-chloro-2-nitrobenzoic acid Chemical compound OC(=O)C1=CC=C(Cl)C=C1[N+]([O-])=O JAHIPDTWWVYVRV-UHFFFAOYSA-N 0.000 claims description 2
- BBYDXOIZLAWGSL-UHFFFAOYSA-N 4-fluorobenzoic acid Chemical compound OC(=O)C1=CC=C(F)C=C1 BBYDXOIZLAWGSL-UHFFFAOYSA-N 0.000 claims description 2
- KDVYCTOWXSLNNI-UHFFFAOYSA-N 4-t-Butylbenzoic acid Chemical compound CC(C)(C)C1=CC=C(C(O)=O)C=C1 KDVYCTOWXSLNNI-UHFFFAOYSA-N 0.000 claims description 2
- ZSIQJIWKELUFRJ-UHFFFAOYSA-N azepane Chemical compound C1CCCNCC1 ZSIQJIWKELUFRJ-UHFFFAOYSA-N 0.000 claims description 2
- JOTRBOXKCFHVLY-UHFFFAOYSA-N ethyl 2-(2-methylindolizin-3-yl)-2-oxoacetate Chemical compound C1=CC=CN2C(C(=O)C(=O)OCC)=C(C)C=C21 JOTRBOXKCFHVLY-UHFFFAOYSA-N 0.000 claims description 2
- AVLBKAHPELJLIA-UHFFFAOYSA-N n,n-diethyl-2-oxo-2-(2-phenylindolizin-3-yl)acetamide Chemical compound C1=C2C=CC=CN2C(C(=O)C(=O)N(CC)CC)=C1C1=CC=CC=C1 AVLBKAHPELJLIA-UHFFFAOYSA-N 0.000 claims description 2
- CINGXKHGZFMCNT-UHFFFAOYSA-N n-(2-cyanopropan-2-yl)-2-oxo-2-(2-phenylindolizin-3-yl)acetamide Chemical compound C1=C2C=CC=CN2C(C(=O)C(=O)NC(C)(C)C#N)=C1C1=CC=CC=C1 CINGXKHGZFMCNT-UHFFFAOYSA-N 0.000 claims description 2
- UKZQBZZYOLHDRO-UHFFFAOYSA-N n-(2-hydroxyethyl)-2-oxo-2-(2-phenylindolizin-3-yl)acetamide Chemical compound C1=C2C=CC=CN2C(C(=O)C(=O)NCCO)=C1C1=CC=CC=C1 UKZQBZZYOLHDRO-UHFFFAOYSA-N 0.000 claims description 2
- MKZJWXANJXXPLT-UHFFFAOYSA-N n-butyl-2-oxo-2-(2-phenylindolizin-3-yl)acetamide Chemical compound C1=C2C=CC=CN2C(C(=O)C(=O)NCCCC)=C1C1=CC=CC=C1 MKZJWXANJXXPLT-UHFFFAOYSA-N 0.000 claims description 2
- VCMVHBHMGOMKBX-UHFFFAOYSA-N n-naphthalen-1-yl-2-oxo-2-(2-phenylindolizin-3-yl)acetamide Chemical compound C=1C=CC2=CC=CC=C2C=1NC(=O)C(=O)C(N1C=CC=CC1=C1)=C1C1=CC=CC=C1 VCMVHBHMGOMKBX-UHFFFAOYSA-N 0.000 claims description 2
- 206010006474 Bronchopulmonary aspergillosis allergic Diseases 0.000 claims 6
- 208000006778 allergic bronchopulmonary aspergillosis Diseases 0.000 claims 6
- ZOUYQLYCEAXYRN-UHFFFAOYSA-N 2-oxo-2-(2-phenylindolizin-3-yl)-n-[3-(trifluoromethyl)phenyl]acetamide Chemical compound FC(F)(F)C1=CC=CC(NC(=O)C(=O)C=2N3C=CC=CC3=CC=2C=2C=CC=CC=2)=C1 ZOUYQLYCEAXYRN-UHFFFAOYSA-N 0.000 claims 4
- 229910052760 oxygen Inorganic materials 0.000 claims 4
- SXYAYOJWQXGLBY-UHFFFAOYSA-N 2-oxo-2-(2-phenylindolizin-3-yl)-n-[4-(trifluoromethyl)phenyl]acetamide Chemical compound C1=CC(C(F)(F)F)=CC=C1NC(=O)C(=O)C1=C(C=2C=CC=CC=2)C=C2N1C=CC=C2 SXYAYOJWQXGLBY-UHFFFAOYSA-N 0.000 claims 3
- VVOGBNCJNXZGND-UHFFFAOYSA-N 2-oxo-n-phenyl-2-(2-phenylindolizin-3-yl)acetamide Chemical compound C=1C=CC=CC=1C=1C=C2C=CC=CN2C=1C(=O)C(=O)NC1=CC=CC=C1 VVOGBNCJNXZGND-UHFFFAOYSA-N 0.000 claims 3
- 241001480043 Arthrodermataceae Species 0.000 claims 3
- 208000006673 asthma Diseases 0.000 claims 3
- 230000037304 dermatophytes Effects 0.000 claims 3
- IMYILLXMUKDUBW-UHFFFAOYSA-N methyl 4-[[2-oxo-2-(2-phenylindolizin-3-yl)acetyl]amino]benzoate Chemical compound C1=CC(C(=O)OC)=CC=C1NC(=O)C(=O)C1=C(C=2C=CC=CC=2)C=C2N1C=CC=C2 IMYILLXMUKDUBW-UHFFFAOYSA-N 0.000 claims 3
- YXPVJQWWVLBNOP-UHFFFAOYSA-N n,n-dimethyl-2-oxo-2-(2-phenylindolizin-3-yl)acetamide Chemical compound C1=C2C=CC=CN2C(C(=O)C(=O)N(C)C)=C1C1=CC=CC=C1 YXPVJQWWVLBNOP-UHFFFAOYSA-N 0.000 claims 3
- CFANDBNQOPWLLG-UHFFFAOYSA-N n-(2,4-dichlorophenyl)-2-oxo-2-(2-phenylindolizin-3-yl)acetamide Chemical compound ClC1=CC(Cl)=CC=C1NC(=O)C(=O)C1=C(C=2C=CC=CC=2)C=C2N1C=CC=C2 CFANDBNQOPWLLG-UHFFFAOYSA-N 0.000 claims 3
- GISHZMOZACETMK-UHFFFAOYSA-N n-(2-methoxyphenyl)-2-oxo-2-(2-phenylindolizin-3-yl)acetamide Chemical compound COC1=CC=CC=C1NC(=O)C(=O)C1=C(C=2C=CC=CC=2)C=C2N1C=CC=C2 GISHZMOZACETMK-UHFFFAOYSA-N 0.000 claims 3
- XLEJTJNAUCHOIW-UHFFFAOYSA-N n-(4-methylphenyl)-2-oxo-2-(2-phenylindolizin-3-yl)acetamide Chemical compound C1=CC(C)=CC=C1NC(=O)C(=O)C1=C(C=2C=CC=CC=2)C=C2N1C=CC=C2 XLEJTJNAUCHOIW-UHFFFAOYSA-N 0.000 claims 3
- HQSZCJFRYCQMER-UHFFFAOYSA-N n-cyclohexyl-2-oxo-2-(2-phenylindolizin-3-yl)acetamide Chemical compound C=1C=CC=CC=1C=1C=C2C=CC=CN2C=1C(=O)C(=O)NC1CCCCC1 HQSZCJFRYCQMER-UHFFFAOYSA-N 0.000 claims 3
- AEQFWFHYBOGHPZ-UHFFFAOYSA-N propyl 4-[[2-oxo-2-(1-phenylindolizin-3-yl)acetyl]amino]benzoate Chemical compound C1=CC(C(=O)OCCC)=CC=C1NC(=O)C(=O)C1=CC(C=2C=CC=CC=2)=C2N1C=CC=C2 AEQFWFHYBOGHPZ-UHFFFAOYSA-N 0.000 claims 3
- SKJILAHJCLXZHK-UHFFFAOYSA-N 1-(2,3-dihydroindol-1-yl)-2-(2-phenylindolizin-3-yl)ethane-1,2-dione Chemical compound C1CC2=CC=CC=C2N1C(=O)C(=O)C(N1C=CC=CC1=C1)=C1C1=CC=CC=C1 SKJILAHJCLXZHK-UHFFFAOYSA-N 0.000 claims 2
- NEQIQFVEMLMFKO-UHFFFAOYSA-N 1-(2-phenylindolizin-3-yl)-2-piperidin-1-ylethane-1,2-dione Chemical compound C=1C=CC=CC=1C=1C=C2C=CC=CN2C=1C(=O)C(=O)N1CCCCC1 NEQIQFVEMLMFKO-UHFFFAOYSA-N 0.000 claims 2
- OFJHPJBBMKQNRN-UHFFFAOYSA-N 2-(6-methoxy-2-phenylindolizin-3-yl)-n-(4-methylphenyl)-2-oxoacetamide Chemical compound N12C=C(OC)C=CC2=CC(C=2C=CC=CC=2)=C1C(=O)C(=O)NC1=CC=C(C)C=C1 OFJHPJBBMKQNRN-UHFFFAOYSA-N 0.000 claims 2
- DLECTVHWNHXKCZ-UHFFFAOYSA-N 2-(6-methoxy-2-phenylindolizin-3-yl)-n-(6-methoxypyridin-3-yl)-2-oxoacetamide Chemical compound N12C=C(OC)C=CC2=CC(C=2C=CC=CC=2)=C1C(=O)C(=O)NC1=CC=C(OC)N=C1 DLECTVHWNHXKCZ-UHFFFAOYSA-N 0.000 claims 2
- LPCQHPQJYLNGCE-UHFFFAOYSA-N 2-(dimethylamino)-5-[[2-oxo-2-(2-phenylindolizin-3-yl)acetyl]amino]benzoic acid Chemical compound C1=C(C(O)=O)C(N(C)C)=CC=C1NC(=O)C(=O)C1=C(C=2C=CC=CC=2)C=C2N1C=CC=C2 LPCQHPQJYLNGCE-UHFFFAOYSA-N 0.000 claims 2
- ZRYFJTKXECOZSL-UHFFFAOYSA-N 2-[2-(2-chlorophenyl)indolizin-3-yl]-n-(2,4-difluorophenyl)-2-oxoacetamide Chemical compound FC1=CC(F)=CC=C1NC(=O)C(=O)C1=C(C=2C(=CC=CC=2)Cl)C=C2N1C=CC=C2 ZRYFJTKXECOZSL-UHFFFAOYSA-N 0.000 claims 2
- DSAYIPBLOUTBDS-UHFFFAOYSA-N 2-[2-(2-methylphenyl)indolizin-3-yl]-2-oxo-n-[6-(2,2,3,3-tetrafluoropropoxy)pyridin-3-yl]acetamide Chemical compound CC1=CC=CC=C1C1=C(C(=O)C(=O)NC=2C=NC(OCC(F)(F)C(F)F)=CC=2)N2C=CC=CC2=C1 DSAYIPBLOUTBDS-UHFFFAOYSA-N 0.000 claims 2
- LIQNIGHEHLQXRR-UHFFFAOYSA-N 2-[2-(2-methylpyridin-3-yl)indolizin-3-yl]-2-oxo-n-[4-(2,2,3,3-tetrafluoropropoxy)phenyl]acetamide Chemical compound CC1=NC=CC=C1C1=C(C(=O)C(=O)NC=2C=CC(OCC(F)(F)C(F)F)=CC=2)N2C=CC=CC2=C1 LIQNIGHEHLQXRR-UHFFFAOYSA-N 0.000 claims 2
- UXFGCDCVAQIRGH-UHFFFAOYSA-N 2-[2-(3-chlorophenyl)indolizin-3-yl]-n-(4-methoxyphenyl)-2-oxoacetamide Chemical compound C1=CC(OC)=CC=C1NC(=O)C(=O)C1=C(C=2C=C(Cl)C=CC=2)C=C2N1C=CC=C2 UXFGCDCVAQIRGH-UHFFFAOYSA-N 0.000 claims 2
- WVZBRCIKIYNRRI-UHFFFAOYSA-N 2-[2-(3-cyanophenyl)indolizin-3-yl]-n-(2,4-difluorophenyl)-2-oxoacetamide Chemical compound FC1=CC(F)=CC=C1NC(=O)C(=O)C1=C(C=2C=C(C=CC=2)C#N)C=C2N1C=CC=C2 WVZBRCIKIYNRRI-UHFFFAOYSA-N 0.000 claims 2
- QBPGDKKCMULZSL-UHFFFAOYSA-N 2-[2-(3-cyanophenyl)indolizin-3-yl]-n-(4-methoxyphenyl)-2-oxoacetamide Chemical compound C1=CC(OC)=CC=C1NC(=O)C(=O)C1=C(C=2C=C(C=CC=2)C#N)C=C2N1C=CC=C2 QBPGDKKCMULZSL-UHFFFAOYSA-N 0.000 claims 2
- FSGZKJKCJVGAQU-UHFFFAOYSA-N 2-[2-(4-fluorophenyl)indolizin-3-yl]-n-(4-methoxyphenyl)-2-oxoacetamide Chemical compound C1=CC(OC)=CC=C1NC(=O)C(=O)C1=C(C=2C=CC(F)=CC=2)C=C2N1C=CC=C2 FSGZKJKCJVGAQU-UHFFFAOYSA-N 0.000 claims 2
- ICUOREAQMDYNIU-UHFFFAOYSA-N 2-[2-(4-fluorophenyl)indolizin-3-yl]-n-(4-methylphenyl)-2-oxoacetamide Chemical compound C1=CC(C)=CC=C1NC(=O)C(=O)C1=C(C=2C=CC(F)=CC=2)C=C2N1C=CC=C2 ICUOREAQMDYNIU-UHFFFAOYSA-N 0.000 claims 2
- YNJZWFPARSWUES-UHFFFAOYSA-N 2-[2-(4-fluorophenyl)indolizin-3-yl]-n-(6-methoxypyridin-3-yl)-2-oxoacetamide Chemical compound C1=NC(OC)=CC=C1NC(=O)C(=O)C1=C(C=2C=CC(F)=CC=2)C=C2N1C=CC=C2 YNJZWFPARSWUES-UHFFFAOYSA-N 0.000 claims 2
- FDXWSHZFMOUAIN-UHFFFAOYSA-N 2-[2-(furan-2-yl)indolizin-3-yl]-n-(4-methoxyphenyl)-2-oxoacetamide Chemical compound C1=CC(OC)=CC=C1NC(=O)C(=O)C1=C(C=2OC=CC=2)C=C2N1C=CC=C2 FDXWSHZFMOUAIN-UHFFFAOYSA-N 0.000 claims 2
- IZAWMWVDJQLKRG-UHFFFAOYSA-N 2-[2-(furan-2-yl)indolizin-3-yl]-n-(4-methylphenyl)-2-oxoacetamide Chemical compound C1=CC(C)=CC=C1NC(=O)C(=O)C1=C(C=2OC=CC=2)C=C2N1C=CC=C2 IZAWMWVDJQLKRG-UHFFFAOYSA-N 0.000 claims 2
- UJHMBNTZEKEBSN-UHFFFAOYSA-N 2-[2-(furan-2-yl)indolizin-3-yl]-n-(6-methoxypyridin-3-yl)-2-oxoacetamide Chemical compound C1=NC(OC)=CC=C1NC(=O)C(=O)C1=C(C=2OC=CC=2)C=C2N1C=CC=C2 UJHMBNTZEKEBSN-UHFFFAOYSA-N 0.000 claims 2
- IDBYKYUSNRMVCE-UHFFFAOYSA-N 2-[3-[[2-oxo-2-(2-phenylindolizin-3-yl)acetyl]amino]phenoxy]acetic acid Chemical compound OC(=O)COC1=CC=CC(NC(=O)C(=O)C=2N3C=CC=CC3=CC=2C=2C=CC=CC=2)=C1 IDBYKYUSNRMVCE-UHFFFAOYSA-N 0.000 claims 2
- WQNUFOQDZDPLBP-UHFFFAOYSA-N 2-oxo-2-(2-phenylindolizin-3-yl)-n-(2,3,4-trimethylphenyl)acetamide Chemical compound CC1=C(C)C(C)=CC=C1NC(=O)C(=O)C1=C(C=2C=CC=CC=2)C=C2N1C=CC=C2 WQNUFOQDZDPLBP-UHFFFAOYSA-N 0.000 claims 2
- KSCWEDYOTDNPLX-UHFFFAOYSA-N 2-oxo-2-(2-phenylindolizin-3-yl)-n-(3,4,5-trimethoxyphenyl)acetamide Chemical compound COC1=C(OC)C(OC)=CC(NC(=O)C(=O)C=2N3C=CC=CC3=CC=2C=2C=CC=CC=2)=C1 KSCWEDYOTDNPLX-UHFFFAOYSA-N 0.000 claims 2
- PNRINBHGNXBPPB-UHFFFAOYSA-N 2-oxo-2-(2-phenylindolizin-3-yl)-n-(4-piperidin-1-ylphenyl)acetamide Chemical compound C=1C=CC=CC=1C=1C=C2C=CC=CN2C=1C(=O)C(=O)NC(C=C1)=CC=C1N1CCCCC1 PNRINBHGNXBPPB-UHFFFAOYSA-N 0.000 claims 2
- NXXVLMRNSVLOKC-UHFFFAOYSA-N 2-oxo-2-(2-phenylindolizin-3-yl)-n-(4-propan-2-ylphenyl)acetamide Chemical compound C1=CC(C(C)C)=CC=C1NC(=O)C(=O)C1=C(C=2C=CC=CC=2)C=C2N1C=CC=C2 NXXVLMRNSVLOKC-UHFFFAOYSA-N 0.000 claims 2
- QOBXNLDGPIWAIM-UHFFFAOYSA-N 2-oxo-2-(2-phenylindolizin-3-yl)-n-(4-pyrrolidin-1-ylphenyl)acetamide Chemical compound C=1C=CC=CC=1C=1C=C2C=CC=CN2C=1C(=O)C(=O)NC(C=C1)=CC=C1N1CCCC1 QOBXNLDGPIWAIM-UHFFFAOYSA-N 0.000 claims 2
- USRWPOGUTQRHRS-UHFFFAOYSA-N 2-oxo-2-(2-phenylindolizin-3-yl)-n-(4-thiomorpholin-4-ylphenyl)acetamide Chemical compound C=1C=CC=CC=1C=1C=C2C=CC=CN2C=1C(=O)C(=O)NC(C=C1)=CC=C1N1CCSCC1 USRWPOGUTQRHRS-UHFFFAOYSA-N 0.000 claims 2
- MAEQTCCZZDPRHR-UHFFFAOYSA-N 2-oxo-2-(2-phenylindolizin-3-yl)-n-[4-(1,3-thiazol-2-yl)phenyl]acetamide Chemical compound C=1C=CC=CC=1C=1C=C2C=CC=CN2C=1C(=O)C(=O)NC(C=C1)=CC=C1C1=NC=CS1 MAEQTCCZZDPRHR-UHFFFAOYSA-N 0.000 claims 2
- KVLBJSWSRKPZKV-UHFFFAOYSA-N 2-oxo-2-(2-phenylindolizin-3-yl)-n-[4-(1,3-thiazol-2-ylamino)phenyl]acetamide Chemical compound C=1C=CC=CC=1C=1C=C2C=CC=CN2C=1C(=O)C(=O)NC(C=C1)=CC=C1NC1=NC=CS1 KVLBJSWSRKPZKV-UHFFFAOYSA-N 0.000 claims 2
- HDMXZQXNCVFQKD-UHFFFAOYSA-N 2-oxo-2-(2-phenylindolizin-3-yl)-n-[4-(2h-tetrazol-5-yl)phenyl]acetamide Chemical compound C=1C=CC=CC=1C=1C=C2C=CC=CN2C=1C(=O)C(=O)NC(C=C1)=CC=C1C1=NN=NN1 HDMXZQXNCVFQKD-UHFFFAOYSA-N 0.000 claims 2
- WQOPOAYIUUOTEK-UHFFFAOYSA-N 2-oxo-2-(2-phenylindolizin-3-yl)-n-[4-(pyridin-2-ylamino)phenyl]acetamide Chemical compound C=1C=CC=CC=1C=1C=C2C=CC=CN2C=1C(=O)C(=O)NC(C=C1)=CC=C1NC1=CC=CC=N1 WQOPOAYIUUOTEK-UHFFFAOYSA-N 0.000 claims 2
- IYBRGCFLXQQGPQ-UHFFFAOYSA-N 2-oxo-2-(2-phenylindolizin-3-yl)-n-[4-(pyrimidin-2-ylamino)phenyl]acetamide Chemical compound C=1C=CC=CC=1C=1C=C2C=CC=CN2C=1C(=O)C(=O)NC(C=C1)=CC=C1NC1=NC=CC=N1 IYBRGCFLXQQGPQ-UHFFFAOYSA-N 0.000 claims 2
- LSUOFOZXCAXECK-UHFFFAOYSA-N 2-oxo-2-(2-phenylindolizin-3-yl)-n-propan-2-ylacetamide Chemical compound C1=C2C=CC=CN2C(C(=O)C(=O)NC(C)C)=C1C1=CC=CC=C1 LSUOFOZXCAXECK-UHFFFAOYSA-N 0.000 claims 2
- ULTHMUNGRUGIKI-UHFFFAOYSA-N 2-oxo-2-(2-phenylindolizin-3-yl)-n-pyridin-2-ylacetamide Chemical compound C=1C=CC=CC=1C=1C=C2C=CC=CN2C=1C(=O)C(=O)NC1=CC=CC=N1 ULTHMUNGRUGIKI-UHFFFAOYSA-N 0.000 claims 2
- AJSVOCLOKYFXBS-UHFFFAOYSA-N 2-oxo-2-(2-phenylindolizin-3-yl)-n-pyridin-3-ylacetamide Chemical compound C=1C=CC=CC=1C=1C=C2C=CC=CN2C=1C(=O)C(=O)NC1=CC=CN=C1 AJSVOCLOKYFXBS-UHFFFAOYSA-N 0.000 claims 2
- NZQQJSXXQLFIJD-UHFFFAOYSA-N 2-oxo-2-(2-phenylindolizin-3-yl)-n-pyridin-4-ylacetamide Chemical compound C=1C=CC=CC=1C=1C=C2C=CC=CN2C=1C(=O)C(=O)NC1=CC=NC=C1 NZQQJSXXQLFIJD-UHFFFAOYSA-N 0.000 claims 2
- UIWJVCHPUGVTKC-UHFFFAOYSA-N 2-oxo-2-(2-pyridin-3-ylindolizin-3-yl)-n-(3,4,5-trimethoxyphenyl)acetamide Chemical compound COC1=C(OC)C(OC)=CC(NC(=O)C(=O)C=2N3C=CC=CC3=CC=2C=2C=NC=CC=2)=C1 UIWJVCHPUGVTKC-UHFFFAOYSA-N 0.000 claims 2
- DHVRYCVEZKWNFZ-UHFFFAOYSA-N 2-oxo-2-(2-pyridin-3-ylindolizin-3-yl)-n-[3-(trifluoromethyl)phenyl]acetamide Chemical compound FC(F)(F)C1=CC=CC(NC(=O)C(=O)C=2N3C=CC=CC3=CC=2C=2C=NC=CC=2)=C1 DHVRYCVEZKWNFZ-UHFFFAOYSA-N 0.000 claims 2
- XZDIUHFXYNAVCI-UHFFFAOYSA-N 2-oxo-2-(2-pyridin-3-ylindolizin-3-yl)-n-[4-(trifluoromethyl)phenyl]acetamide Chemical compound C1=CC(C(F)(F)F)=CC=C1NC(=O)C(=O)C1=C(C=2C=NC=CC=2)C=C2N1C=CC=C2 XZDIUHFXYNAVCI-UHFFFAOYSA-N 0.000 claims 2
- DXXCVMDVZOVPHS-UHFFFAOYSA-N 2-oxo-n-[4-(2-oxopropyl)phenyl]-2-(2-phenylindolizin-3-yl)acetamide Chemical compound C1=CC(CC(=O)C)=CC=C1NC(=O)C(=O)C1=C(C=2C=CC=CC=2)C=C2N1C=CC=C2 DXXCVMDVZOVPHS-UHFFFAOYSA-N 0.000 claims 2
- XLSQMTFMFQCTSH-UHFFFAOYSA-N 2-oxo-n-[4-(4-oxopiperidin-1-yl)phenyl]-2-(2-phenylindolizin-3-yl)acetamide Chemical compound C=1C=CC=CC=1C=1C=C2C=CC=CN2C=1C(=O)C(=O)NC(C=C1)=CC=C1N1CCC(=O)CC1 XLSQMTFMFQCTSH-UHFFFAOYSA-N 0.000 claims 2
- DAGVXGKPGZWOOH-UHFFFAOYSA-N 4-[[2-oxo-2-(2-phenylindolizin-3-yl)acetyl]amino]benzamide Chemical compound C1=CC(C(=O)N)=CC=C1NC(=O)C(=O)C1=C(C=2C=CC=CC=2)C=C2N1C=CC=C2 DAGVXGKPGZWOOH-UHFFFAOYSA-N 0.000 claims 2
- OVOYYDRYDCGAJI-UHFFFAOYSA-N 4-[[2-oxo-2-(2-phenylindolizin-3-yl)acetyl]amino]benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1NC(=O)C(=O)C1=C(C=2C=CC=CC=2)C=C2N1C=CC=C2 OVOYYDRYDCGAJI-UHFFFAOYSA-N 0.000 claims 2
- 229910006069 SO3H Inorganic materials 0.000 claims 2
- PVUXPEYLCQIEBI-UHFFFAOYSA-N [3-[[2-oxo-2-(2-phenylindolizin-3-yl)acetyl]amino]phenyl] n,n-diethylcarbamate Chemical compound CCN(CC)C(=O)OC1=CC=CC(NC(=O)C(=O)C=2N3C=CC=CC3=CC=2C=2C=CC=CC=2)=C1 PVUXPEYLCQIEBI-UHFFFAOYSA-N 0.000 claims 2
- YHMDAABDBXUAJA-UHFFFAOYSA-N butyl 4-[[2-oxo-2-(2-phenylindolizin-3-yl)acetyl]amino]benzoate Chemical compound C1=CC(C(=O)OCCCC)=CC=C1NC(=O)C(=O)C1=C(C=2C=CC=CC=2)C=C2N1C=CC=C2 YHMDAABDBXUAJA-UHFFFAOYSA-N 0.000 claims 2
- 125000004432 carbon atom Chemical group C* 0.000 claims 2
- QWDRSWCSMOJUJX-UHFFFAOYSA-N ethyl 2-[[2-oxo-2-(2-phenylindolizin-3-yl)acetyl]amino]benzoate Chemical compound CCOC(=O)C1=CC=CC=C1NC(=O)C(=O)C1=C(C=2C=CC=CC=2)C=C2N1C=CC=C2 QWDRSWCSMOJUJX-UHFFFAOYSA-N 0.000 claims 2
- FBQSDVMGHHUCDC-UHFFFAOYSA-N ethyl 2-methyl-2-[[2-oxo-2-(2-phenylindolizin-3-yl)acetyl]amino]-3-phenylpropanoate Chemical compound C=1C=CC=CC=1C=1C=C2C=CC=CN2C=1C(=O)C(=O)NC(C)(C(=O)OCC)CC1=CC=CC=C1 FBQSDVMGHHUCDC-UHFFFAOYSA-N 0.000 claims 2
- FTOYBPJSGLTMNQ-UHFFFAOYSA-N ethyl 2-methyl-2-[[2-oxo-2-(2-phenylindolizin-3-yl)acetyl]amino]propanoate Chemical compound C1=C2C=CC=CN2C(C(=O)C(=O)NC(C)(C)C(=O)OCC)=C1C1=CC=CC=C1 FTOYBPJSGLTMNQ-UHFFFAOYSA-N 0.000 claims 2
- IQUDVNVKJJZCIU-UHFFFAOYSA-N methyl 2-[[2-oxo-2-(2-phenylindolizin-3-yl)acetyl]amino]benzoate Chemical compound COC(=O)C1=CC=CC=C1NC(=O)C(=O)C1=C(C=2C=CC=CC=2)C=C2N1C=CC=C2 IQUDVNVKJJZCIU-UHFFFAOYSA-N 0.000 claims 2
- YQIXUWYJVKFVSO-UHFFFAOYSA-N methyl 3-[[2-oxo-2-(2-phenylindolizin-3-yl)acetyl]amino]benzoate Chemical compound COC(=O)C1=CC=CC(NC(=O)C(=O)C=2N3C=CC=CC3=CC=2C=2C=CC=CC=2)=C1 YQIXUWYJVKFVSO-UHFFFAOYSA-N 0.000 claims 2
- ZRMUYIHIKARZHI-UHFFFAOYSA-N methyl 4-[2-oxo-2-(2-phenylindolizin-3-yl)acetyl]oxybenzoate Chemical compound C1=CC(C(=O)OC)=CC=C1OC(=O)C(=O)C1=C(C=2C=CC=CC=2)C=C2N1C=CC=C2 ZRMUYIHIKARZHI-UHFFFAOYSA-N 0.000 claims 2
- GRMFSESMZPKVJL-UHFFFAOYSA-N methyl 5-[[2-oxo-2-(2-phenylindolizin-3-yl)acetyl]amino]thiophene-3-carboxylate Chemical compound COC(=O)C1=CSC(NC(=O)C(=O)C=2N3C=CC=CC3=CC=2C=2C=CC=CC=2)=C1 GRMFSESMZPKVJL-UHFFFAOYSA-N 0.000 claims 2
- KSJKURXUWMAUEN-UHFFFAOYSA-N n-(1-methyl-2,3-dihydroindol-5-yl)-2-oxo-2-(2-phenylindolizin-3-yl)acetamide Chemical compound C=1C=C2N(C)CCC2=CC=1NC(=O)C(=O)C(N1C=CC=CC1=C1)=C1C1=CC=CC=C1 KSJKURXUWMAUEN-UHFFFAOYSA-N 0.000 claims 2
- DWTVGGGTVGVQCQ-UHFFFAOYSA-N n-(1-methylbenzimidazol-5-yl)-2-oxo-2-(2-phenylindolizin-3-yl)acetamide Chemical compound C=1C=C2N(C)C=NC2=CC=1NC(=O)C(=O)C(N1C=CC=CC1=C1)=C1C1=CC=CC=C1 DWTVGGGTVGVQCQ-UHFFFAOYSA-N 0.000 claims 2
- YGCJFFJZKOCISN-UHFFFAOYSA-N n-(1-methylindol-5-yl)-2-oxo-2-(2-phenylindolizin-3-yl)acetamide Chemical compound C=1C=C2N(C)C=CC2=CC=1NC(=O)C(=O)C(N1C=CC=CC1=C1)=C1C1=CC=CC=C1 YGCJFFJZKOCISN-UHFFFAOYSA-N 0.000 claims 2
- CZXFGBIEFJDFHR-UHFFFAOYSA-N n-(2,4-dichlorophenyl)-2-oxo-2-(2-pyridin-3-ylindolizin-3-yl)acetamide Chemical compound ClC1=CC(Cl)=CC=C1NC(=O)C(=O)C1=C(C=2C=NC=CC=2)C=C2N1C=CC=C2 CZXFGBIEFJDFHR-UHFFFAOYSA-N 0.000 claims 2
- VLOYTVDWLDMEPM-UHFFFAOYSA-N n-(2,4-difluorophenyl)-2-[2-(2,4-difluorophenyl)indolizin-3-yl]-2-oxoacetamide Chemical compound FC1=CC(F)=CC=C1NC(=O)C(=O)C1=C(C=2C(=CC(F)=CC=2)F)C=C2N1C=CC=C2 VLOYTVDWLDMEPM-UHFFFAOYSA-N 0.000 claims 2
- VXMGGMVKVCQAQI-UHFFFAOYSA-N n-(2,4-difluorophenyl)-2-[2-(2-methoxyphenyl)indolizin-3-yl]-2-oxoacetamide Chemical compound COC1=CC=CC=C1C1=C(C(=O)C(=O)NC=2C(=CC(F)=CC=2)F)N2C=CC=CC2=C1 VXMGGMVKVCQAQI-UHFFFAOYSA-N 0.000 claims 2
- WZUMNBVDVNLDRS-UHFFFAOYSA-N n-(2,4-difluorophenyl)-2-[2-(3-fluorophenyl)indolizin-3-yl]-2-oxoacetamide Chemical compound FC1=CC=CC(C2=C(N3C=CC=CC3=C2)C(=O)C(=O)NC=2C(=CC(F)=CC=2)F)=C1 WZUMNBVDVNLDRS-UHFFFAOYSA-N 0.000 claims 2
- UKKHEYNTLUBNCX-UHFFFAOYSA-N n-(2,4-dimethoxyphenyl)-2-[2-(4-fluorophenyl)indolizin-3-yl]-2-oxoacetamide Chemical compound COC1=CC(OC)=CC=C1NC(=O)C(=O)C1=C(C=2C=CC(F)=CC=2)C=C2N1C=CC=C2 UKKHEYNTLUBNCX-UHFFFAOYSA-N 0.000 claims 2
- IMVYGRRMNHQDMZ-UHFFFAOYSA-N n-(2,4-dimethoxyphenyl)-2-[2-(furan-2-yl)indolizin-3-yl]-2-oxoacetamide Chemical compound COC1=CC(OC)=CC=C1NC(=O)C(=O)C1=C(C=2OC=CC=2)C=C2N1C=CC=C2 IMVYGRRMNHQDMZ-UHFFFAOYSA-N 0.000 claims 2
- CVZVGLNJRGMFTK-UHFFFAOYSA-N n-(2,4-dimethoxyphenyl)-2-oxo-2-(2-pyridin-2-ylindolizin-3-yl)acetamide Chemical compound COC1=CC(OC)=CC=C1NC(=O)C(=O)C1=C(C=2N=CC=CC=2)C=C2N1C=CC=C2 CVZVGLNJRGMFTK-UHFFFAOYSA-N 0.000 claims 2
- YEPFVMKIBOCFTH-UHFFFAOYSA-N n-(2,4-dimethoxyphenyl)-2-oxo-2-(2-pyridin-3-ylindolizin-3-yl)acetamide Chemical compound COC1=CC(OC)=CC=C1NC(=O)C(=O)C1=C(C=2C=NC=CC=2)C=C2N1C=CC=C2 YEPFVMKIBOCFTH-UHFFFAOYSA-N 0.000 claims 2
- KOSVQOYHHPSCPF-UHFFFAOYSA-N n-(2,4-dimethoxyphenyl)-2-oxo-2-(2-pyridin-4-ylindolizin-3-yl)acetamide Chemical compound COC1=CC(OC)=CC=C1NC(=O)C(=O)C1=C(C=2C=CN=CC=2)C=C2N1C=CC=C2 KOSVQOYHHPSCPF-UHFFFAOYSA-N 0.000 claims 2
- GFXUSGOHNLYLCM-UHFFFAOYSA-N n-(2,4-dimethoxyphenyl)-2-oxo-2-(2-thiophen-2-ylindolizin-3-yl)acetamide Chemical compound COC1=CC(OC)=CC=C1NC(=O)C(=O)C1=C(C=2SC=CC=2)C=C2N1C=CC=C2 GFXUSGOHNLYLCM-UHFFFAOYSA-N 0.000 claims 2
- OSKXBTZEGSXZRU-UHFFFAOYSA-N n-(2-chlorophenyl)-2-oxo-2-(2-phenylindolizin-3-yl)acetamide Chemical compound ClC1=CC=CC=C1NC(=O)C(=O)C1=C(C=2C=CC=CC=2)C=C2N1C=CC=C2 OSKXBTZEGSXZRU-UHFFFAOYSA-N 0.000 claims 2
- QMWQSBCQTFZDGP-UHFFFAOYSA-N n-(2-chlorophenyl)-2-oxo-2-(2-pyridin-3-ylindolizin-3-yl)acetamide Chemical compound ClC1=CC=CC=C1NC(=O)C(=O)C1=C(C=2C=NC=CC=2)C=C2N1C=CC=C2 QMWQSBCQTFZDGP-UHFFFAOYSA-N 0.000 claims 2
- QMKBNEPVVXINKE-UHFFFAOYSA-N n-(2-fluorophenyl)-2-oxo-2-(2-phenylindolizin-3-yl)acetamide Chemical compound FC1=CC=CC=C1NC(=O)C(=O)C1=C(C=2C=CC=CC=2)C=C2N1C=CC=C2 QMKBNEPVVXINKE-UHFFFAOYSA-N 0.000 claims 2
- FWJLGAGCVLTPKZ-UHFFFAOYSA-N n-(2-fluorophenyl)-2-oxo-2-(2-pyridin-3-ylindolizin-3-yl)acetamide Chemical compound FC1=CC=CC=C1NC(=O)C(=O)C1=C(C=2C=NC=CC=2)C=C2N1C=CC=C2 FWJLGAGCVLTPKZ-UHFFFAOYSA-N 0.000 claims 2
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- PIFNVAIKTSIAMR-UHFFFAOYSA-N n-(2-methylphenyl)-2-oxo-2-(2-pyridin-3-ylindolizin-3-yl)acetamide Chemical compound CC1=CC=CC=C1NC(=O)C(=O)C1=C(C=2C=NC=CC=2)C=C2N1C=CC=C2 PIFNVAIKTSIAMR-UHFFFAOYSA-N 0.000 claims 2
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- BNEVWVBOHNLWOK-UHFFFAOYSA-N n-(3,5-dichlorophenyl)-2-oxo-2-(2-pyridin-3-ylindolizin-3-yl)acetamide Chemical compound ClC1=CC(Cl)=CC(NC(=O)C(=O)C=2N3C=CC=CC3=CC=2C=2C=NC=CC=2)=C1 BNEVWVBOHNLWOK-UHFFFAOYSA-N 0.000 claims 2
- BZCUNNPJUVOFQK-UHFFFAOYSA-N n-(3-acetyl-4-methoxyphenyl)-2-oxo-2-(2-phenylindolizin-3-yl)acetamide Chemical compound C1=C(C(C)=O)C(OC)=CC=C1NC(=O)C(=O)C1=C(C=2C=CC=CC=2)C=C2N1C=CC=C2 BZCUNNPJUVOFQK-UHFFFAOYSA-N 0.000 claims 2
- FXBQSIWLTOHRMX-UHFFFAOYSA-N n-(3-acetylphenyl)-2-oxo-2-(2-phenylindolizin-3-yl)acetamide Chemical compound CC(=O)C1=CC=CC(NC(=O)C(=O)C=2N3C=CC=CC3=CC=2C=2C=CC=CC=2)=C1 FXBQSIWLTOHRMX-UHFFFAOYSA-N 0.000 claims 2
- MBRCMXJKAVILMR-UHFFFAOYSA-N n-(3-methoxyphenyl)-2-oxo-2-(2-phenylindolizin-3-yl)acetamide Chemical compound COC1=CC=CC(NC(=O)C(=O)C=2N3C=CC=CC3=CC=2C=2C=CC=CC=2)=C1 MBRCMXJKAVILMR-UHFFFAOYSA-N 0.000 claims 2
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- HTDNCMMGWZWIOL-UHFFFAOYSA-N n-(3-methylphenyl)-2-oxo-2-(2-phenylindolizin-3-yl)acetamide Chemical compound CC1=CC=CC(NC(=O)C(=O)C=2N3C=CC=CC3=CC=2C=2C=CC=CC=2)=C1 HTDNCMMGWZWIOL-UHFFFAOYSA-N 0.000 claims 2
- RTODEMVIVHXHLL-UHFFFAOYSA-N n-(3-methylphenyl)-2-oxo-2-(2-pyridin-3-ylindolizin-3-yl)acetamide Chemical compound CC1=CC=CC(NC(=O)C(=O)C=2N3C=CC=CC3=CC=2C=2C=NC=CC=2)=C1 RTODEMVIVHXHLL-UHFFFAOYSA-N 0.000 claims 2
- HMNKCAAUECDIGN-UHFFFAOYSA-N n-(4-acetylphenyl)-2-oxo-2-(2-phenylindolizin-3-yl)acetamide Chemical compound C1=CC(C(=O)C)=CC=C1NC(=O)C(=O)C1=C(C=2C=CC=CC=2)C=C2N1C=CC=C2 HMNKCAAUECDIGN-UHFFFAOYSA-N 0.000 claims 2
- TXFGQDLROXFMRN-UHFFFAOYSA-N n-(4-acetylphenyl)-2-oxo-2-(2-pyridin-3-ylindolizin-3-yl)acetamide Chemical compound C1=CC(C(=O)C)=CC=C1NC(=O)C(=O)C1=C(C=2C=NC=CC=2)C=C2N1C=CC=C2 TXFGQDLROXFMRN-UHFFFAOYSA-N 0.000 claims 2
- YQTHVTOTKUDOML-UHFFFAOYSA-N n-(4-bromophenyl)-2-oxo-2-(2-phenylindolizin-3-yl)acetamide Chemical compound C1=CC(Br)=CC=C1NC(=O)C(=O)C1=C(C=2C=CC=CC=2)C=C2N1C=CC=C2 YQTHVTOTKUDOML-UHFFFAOYSA-N 0.000 claims 2
- LWCYHGHMNDCWAJ-UHFFFAOYSA-N n-(4-bromophenyl)-2-oxo-2-(2-pyridin-3-ylindolizin-3-yl)acetamide Chemical compound C1=CC(Br)=CC=C1NC(=O)C(=O)C1=C(C=2C=NC=CC=2)C=C2N1C=CC=C2 LWCYHGHMNDCWAJ-UHFFFAOYSA-N 0.000 claims 2
- XDEOERZCLUTQST-UHFFFAOYSA-N n-(4-chlorophenyl)-2-[2-(4-fluorophenyl)indolizin-3-yl]-2-oxoacetamide Chemical compound C1=CC(F)=CC=C1C1=C(C(=O)C(=O)NC=2C=CC(Cl)=CC=2)N2C=CC=CC2=C1 XDEOERZCLUTQST-UHFFFAOYSA-N 0.000 claims 2
- FZHFYBXBJAOEFH-UHFFFAOYSA-N n-(4-chlorophenyl)-2-oxo-2-(2-phenylindolizin-3-yl)acetamide Chemical compound C1=CC(Cl)=CC=C1NC(=O)C(=O)C1=C(C=2C=CC=CC=2)C=C2N1C=CC=C2 FZHFYBXBJAOEFH-UHFFFAOYSA-N 0.000 claims 2
- FCHZOXRGAQKEDE-UHFFFAOYSA-N n-(4-chlorophenyl)-2-oxo-2-(2-pyridin-3-ylindolizin-3-yl)acetamide Chemical compound C1=CC(Cl)=CC=C1NC(=O)C(=O)C1=C(C=2C=NC=CC=2)C=C2N1C=CC=C2 FCHZOXRGAQKEDE-UHFFFAOYSA-N 0.000 claims 2
- DPJAJLQCZXCGQQ-UHFFFAOYSA-N n-(4-cyanophenyl)-2-oxo-2-(2-phenylindolizin-3-yl)acetamide Chemical compound C=1C=CC=CC=1C=1C=C2C=CC=CN2C=1C(=O)C(=O)NC1=CC=C(C#N)C=C1 DPJAJLQCZXCGQQ-UHFFFAOYSA-N 0.000 claims 2
- JSESTMQDHXVHBR-UHFFFAOYSA-N n-(4-fluorophenyl)-2-[2-(4-fluorophenyl)indolizin-3-yl]-2-oxoacetamide Chemical compound C1=CC(F)=CC=C1NC(=O)C(=O)C1=C(C=2C=CC(F)=CC=2)C=C2N1C=CC=C2 JSESTMQDHXVHBR-UHFFFAOYSA-N 0.000 claims 2
- XSCYSFXYPHXOPL-UHFFFAOYSA-N n-(4-fluorophenyl)-2-oxo-2-(2-phenylindolizin-3-yl)acetamide Chemical compound C1=CC(F)=CC=C1NC(=O)C(=O)C1=C(C=2C=CC=CC=2)C=C2N1C=CC=C2 XSCYSFXYPHXOPL-UHFFFAOYSA-N 0.000 claims 2
- JOKKYYBHMBDSCM-UHFFFAOYSA-N n-(4-fluorophenyl)-2-oxo-2-(2-pyridin-3-ylindolizin-3-yl)acetamide Chemical compound C1=CC(F)=CC=C1NC(=O)C(=O)C1=C(C=2C=NC=CC=2)C=C2N1C=CC=C2 JOKKYYBHMBDSCM-UHFFFAOYSA-N 0.000 claims 2
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- SJLHNQXOKCGYDY-UHFFFAOYSA-N n-(4-methylphenyl)-2-(5-methyl-2-phenylindolizin-3-yl)-2-oxoacetamide Chemical compound C1=CC(C)=CC=C1NC(=O)C(=O)C1=C(C=2C=CC=CC=2)C=C2N1C(C)=CC=C2 SJLHNQXOKCGYDY-UHFFFAOYSA-N 0.000 claims 2
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- ZVRDMMJZAQITFH-UHFFFAOYSA-N n-[4-(dimethylamino)phenyl]-2-oxo-2-(2-pyridin-3-ylindolizin-3-yl)acetamide Chemical compound C1=CC(N(C)C)=CC=C1NC(=O)C(=O)C1=C(C=2C=NC=CC=2)C=C2N1C=CC=C2 ZVRDMMJZAQITFH-UHFFFAOYSA-N 0.000 claims 2
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- LAOFOXJCELRZQG-UHFFFAOYSA-N n-[6-(dimethylamino)pyridin-3-yl]-2-oxo-2-(2-pyridin-3-ylindolizin-3-yl)acetamide Chemical compound C1=NC(N(C)C)=CC=C1NC(=O)C(=O)C1=C(C=2C=NC=CC=2)C=C2N1C=CC=C2 LAOFOXJCELRZQG-UHFFFAOYSA-N 0.000 claims 2
- QBNCRHNZZSNXTG-UHFFFAOYSA-N n-[6-(dipropylamino)pyridin-3-yl]-2-oxo-2-(2-phenylindolizin-3-yl)acetamide Chemical compound C1=NC(N(CCC)CCC)=CC=C1NC(=O)C(=O)C1=C(C=2C=CC=CC=2)C=C2N1C=CC=C2 QBNCRHNZZSNXTG-UHFFFAOYSA-N 0.000 claims 2
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- NTNTYQHDOKPZFM-UHFFFAOYSA-N n-methyl-2-oxo-n-phenyl-2-(2-pyridin-3-ylindolizin-3-yl)acetamide Chemical compound C=1C=CC=CC=1N(C)C(=O)C(=O)C(N1C=CC=CC1=C1)=C1C1=CC=CN=C1 NTNTYQHDOKPZFM-UHFFFAOYSA-N 0.000 claims 2
- QMSLLKXDYBYHIR-UHFFFAOYSA-N n-methyl-4-[[2-oxo-2-(2-phenylindolizin-3-yl)acetyl]amino]benzamide Chemical compound C1=CC(C(=O)NC)=CC=C1NC(=O)C(=O)C1=C(C=2C=CC=CC=2)C=C2N1C=CC=C2 QMSLLKXDYBYHIR-UHFFFAOYSA-N 0.000 claims 2
- NWFXGAZYUFDHNS-UHFFFAOYSA-N s-(2-methoxyphenyl) 2-oxo-2-(2-phenylindolizin-3-yl)ethanethioate Chemical compound COC1=CC=CC=C1SC(=O)C(=O)C1=C(C=2C=CC=CC=2)C=C2N1C=CC=C2 NWFXGAZYUFDHNS-UHFFFAOYSA-N 0.000 claims 2
- 125000003107 substituted aryl group Chemical group 0.000 claims 2
- 125000005346 substituted cycloalkyl group Chemical group 0.000 claims 2
- RPYUSNQSSONIFG-UHFFFAOYSA-N (2-fluorophenyl)methyl 2-[2-(4-chlorophenyl)indolizin-3-yl]-2-oxoacetate Chemical compound FC1=CC=CC=C1COC(=O)C(=O)C1=C(C=2C=CC(Cl)=CC=2)C=C2N1C=CC=C2 RPYUSNQSSONIFG-UHFFFAOYSA-N 0.000 claims 1
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- FXZUFTUKTFBYBC-UHFFFAOYSA-N 1-(6,7-dimethoxy-3,4-dihydro-1h-isoquinolin-2-yl)-2-(2-phenylindolizin-3-yl)ethane-1,2-dione Chemical compound C1C=2C=C(OC)C(OC)=CC=2CCN1C(=O)C(=O)C(N1C=CC=CC1=C1)=C1C1=CC=CC=C1 FXZUFTUKTFBYBC-UHFFFAOYSA-N 0.000 claims 1
- RBTHGVFCSHNIJP-UHFFFAOYSA-N 1-(azepan-1-yl)-2-(2-phenylindolizin-3-yl)ethane-1,2-dione Chemical compound C=1C=CC=CC=1C=1C=C2C=CC=CN2C=1C(=O)C(=O)N1CCCCCC1 RBTHGVFCSHNIJP-UHFFFAOYSA-N 0.000 claims 1
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- SFIMTHAWYOMCDU-UHFFFAOYSA-N 2-[1-(4-chlorophenyl)-2-(4-nitrophenyl)indolizin-3-yl]-2-oxoacetic acid Chemical compound C=12C=CC=CN2C(C(=O)C(=O)O)=C(C=2C=CC(=CC=2)[N+]([O-])=O)C=1C1=CC=C(Cl)C=C1 SFIMTHAWYOMCDU-UHFFFAOYSA-N 0.000 claims 1
- QPEHMOVUHVYNEB-UHFFFAOYSA-N 2-[2-(4-bromophenyl)-1-(4-chlorophenyl)indolizin-3-yl]-2-oxoacetic acid;ethyl 2-[2-(4-bromophenyl)-1-(4-chlorophenyl)indolizin-3-yl]-2-oxoacetate Chemical compound C=12C=CC=CN2C(C(=O)C(=O)O)=C(C=2C=CC(Br)=CC=2)C=1C1=CC=C(Cl)C=C1.C=12C=CC=CN2C(C(=O)C(=O)OCC)=C(C=2C=CC(Br)=CC=2)C=1C1=CC=C(Cl)C=C1 QPEHMOVUHVYNEB-UHFFFAOYSA-N 0.000 claims 1
- SEGRQDQSHCHEEM-UHFFFAOYSA-N 2-[2-(4-bromophenyl)-1-phenylindolizin-3-yl]-2-oxoacetic acid Chemical compound C=12C=CC=CN2C(C(=O)C(=O)O)=C(C=2C=CC(Br)=CC=2)C=1C1=CC=CC=C1 SEGRQDQSHCHEEM-UHFFFAOYSA-N 0.000 claims 1
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- MCIAVMOXKZRQGC-UHFFFAOYSA-N 2-[2-(4-nitrophenyl)-1-phenylindolizin-3-yl]-2-oxoacetic acid Chemical compound C=12C=CC=CN2C(C(=O)C(=O)O)=C(C=2C=CC(=CC=2)[N+]([O-])=O)C=1C1=CC=CC=C1 MCIAVMOXKZRQGC-UHFFFAOYSA-N 0.000 claims 1
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- TXBGINIXNYGYHC-UHFFFAOYSA-N 2-oxo-2-(2-phenylindolizin-3-yl)-n-(1,2,4-triazol-4-yl)acetamide Chemical compound C=1C=CC=CC=1C=1C=C2C=CC=CN2C=1C(=O)C(=O)NN1C=NN=C1 TXBGINIXNYGYHC-UHFFFAOYSA-N 0.000 claims 1
- HXGLFHFVSBXKMU-UHFFFAOYSA-N 2-oxo-2-(2-phenylindolizin-3-yl)-n-(1,3-thiazol-2-yl)acetamide Chemical compound C=1C=CC=CC=1C=1C=C2C=CC=CN2C=1C(=O)C(=O)NC1=NC=CS1 HXGLFHFVSBXKMU-UHFFFAOYSA-N 0.000 claims 1
- PKKJUUUBNDOBPN-UHFFFAOYSA-N 2-oxo-2-(2-phenylindolizin-3-yl)-n-(4,5,6,7-tetrahydro-1,3-benzothiazol-2-yl)acetamide Chemical compound N=1C=2CCCCC=2SC=1NC(=O)C(=O)C(N1C=CC=CC1=C1)=C1C1=CC=CC=C1 PKKJUUUBNDOBPN-UHFFFAOYSA-N 0.000 claims 1
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- BPASXPPVZGCWCP-UHFFFAOYSA-N 2-oxo-2-(2-phenylindolizin-3-yl)-n-[2-(4-sulfamoylphenyl)ethyl]acetamide Chemical compound C1=CC(S(=O)(=O)N)=CC=C1CCNC(=O)C(=O)C1=C(C=2C=CC=CC=2)C=C2N1C=CC=C2 BPASXPPVZGCWCP-UHFFFAOYSA-N 0.000 claims 1
- RCUZWHUNQQBKBT-UHFFFAOYSA-N 2-oxo-2-(2-phenylindolizin-3-yl)acetamide Chemical compound C1=C2C=CC=CN2C(C(=O)C(=O)N)=C1C1=CC=CC=C1 RCUZWHUNQQBKBT-UHFFFAOYSA-N 0.000 claims 1
- KNJRLSHZEHQWFY-UHFFFAOYSA-N 2-oxo-n-[(3-phenoxyphenyl)methyl]-2-(2-phenylindolizin-3-yl)acetamide Chemical compound C=1C=CC=CC=1C=1C=C2C=CC=CN2C=1C(=O)C(=O)NCC(C=1)=CC=CC=1OC1=CC=CC=C1 KNJRLSHZEHQWFY-UHFFFAOYSA-N 0.000 claims 1
- CKBSCORJPADYHV-UHFFFAOYSA-N 3-[[2-oxo-2-(2-phenylindolizin-3-yl)acetyl]amino]propyl 2,3-dichlorobenzoate Chemical compound ClC1=CC=CC(C(=O)OCCCNC(=O)C(=O)C=2N3C=CC=CC3=CC=2C=2C=CC=CC=2)=C1Cl CKBSCORJPADYHV-UHFFFAOYSA-N 0.000 claims 1
- UTKIKKFIHIKCHN-UHFFFAOYSA-N 3-[[2-oxo-2-(2-phenylindolizin-3-yl)acetyl]amino]propyl 3,4-dichlorobenzoate Chemical compound C1=C(Cl)C(Cl)=CC=C1C(=O)OCCCNC(=O)C(=O)C1=C(C=2C=CC=CC=2)C=C2N1C=CC=C2 UTKIKKFIHIKCHN-UHFFFAOYSA-N 0.000 claims 1
- HTDXXWRFKMETQH-UHFFFAOYSA-N CC=1C=C2C=CC=C(N2C1C(C(C)=O)=NO)C.CC=1N2C(=C(C=C2C=CC1)C1=CC=CC=C1)C(C(=O)C1=CC=CC=C1)=NO.CC=1C=C2C=CC=C(N2C1C(C(=O)C1=CC=CC=C1)=NO)C Chemical compound CC=1C=C2C=CC=C(N2C1C(C(C)=O)=NO)C.CC=1N2C(=C(C=C2C=CC1)C1=CC=CC=C1)C(C(=O)C1=CC=CC=C1)=NO.CC=1C=C2C=CC=C(N2C1C(C(=O)C1=CC=CC=C1)=NO)C HTDXXWRFKMETQH-UHFFFAOYSA-N 0.000 claims 1
- ZSPOTEACELFISG-UHFFFAOYSA-N CC=1N2C(=C(C=C2C=CC1)C1=CC=CC=C1)C(C(C)=O)=NO.CC=1N2C(=C(C=C2C=CC1)C1=CC=CC=C1)C(C(C)=O)=O.O=C(C(=O)NC1=CC=C(C=C1)N1CCCCC1)C1=C(C=C2C=CC=CN12)C1=CC=CC=C1 Chemical compound CC=1N2C(=C(C=C2C=CC1)C1=CC=CC=C1)C(C(C)=O)=NO.CC=1N2C(=C(C=C2C=CC1)C1=CC=CC=C1)C(C(C)=O)=O.O=C(C(=O)NC1=CC=C(C=C1)N1CCCCC1)C1=C(C=C2C=CC=CN12)C1=CC=CC=C1 ZSPOTEACELFISG-UHFFFAOYSA-N 0.000 claims 1
- JHLOJAPUTPOUTJ-UHFFFAOYSA-N N-[2-chloro-5-(4-morpholinylsulfonyl)phenyl]-2-oxo-2-(2-phenyl-3-indolizinyl)acetamide Chemical compound ClC1=CC=C(S(=O)(=O)N2CCOCC2)C=C1NC(=O)C(=O)C(N1C=CC=CC1=C1)=C1C1=CC=CC=C1 JHLOJAPUTPOUTJ-UHFFFAOYSA-N 0.000 claims 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims 1
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- KYDSOJANKXBYIN-UHFFFAOYSA-N ethyl 2-[2-(4-nitrophenyl)-1-phenylindolizin-3-yl]-2-oxoacetate Chemical compound C=12C=CC=CN2C(C(=O)C(=O)OCC)=C(C=2C=CC(=CC=2)[N+]([O-])=O)C=1C1=CC=CC=C1 KYDSOJANKXBYIN-UHFFFAOYSA-N 0.000 claims 1
- UJEFFMUDVGDCGW-UHFFFAOYSA-N methyl 1-[4-[[2-oxo-2-(2-phenylindolizin-3-yl)acetyl]amino]phenyl]pyrrolidine-2-carboxylate Chemical compound COC(=O)C1CCCN1C(C=C1)=CC=C1NC(=O)C(=O)C1=C(C=2C=CC=CC=2)C=C2N1C=CC=C2 UJEFFMUDVGDCGW-UHFFFAOYSA-N 0.000 claims 1
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- ASIZHBAGRDUDCK-UHFFFAOYSA-N n-[2-(dimethylamino)ethyl]-2-oxo-2-(2-phenylindolizin-3-yl)acetamide Chemical compound C1=C2C=CC=CN2C(C(=O)C(=O)NCCN(C)C)=C1C1=CC=CC=C1 ASIZHBAGRDUDCK-UHFFFAOYSA-N 0.000 claims 1
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- QNFKCGSNBRVOJR-UHFFFAOYSA-N n-tert-butyl-2-oxo-2-(2-phenylindolizin-3-yl)acetamide Chemical compound C1=C2C=CC=CN2C(C(=O)C(=O)NC(C)(C)C)=C1C1=CC=CC=C1 QNFKCGSNBRVOJR-UHFFFAOYSA-N 0.000 claims 1
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 claims 1
- 238000002560 therapeutic procedure Methods 0.000 abstract description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 240
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- 125000004365 octenyl group Chemical group C(=CCCCCCC)* 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000005069 octynyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C#C* 0.000 description 1
- 239000004006 olive oil Substances 0.000 description 1
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- 150000002895 organic esters Chemical class 0.000 description 1
- 230000003204 osmotic effect Effects 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
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- 230000000149 penetrating effect Effects 0.000 description 1
- 125000002255 pentenyl group Chemical group C(=CCCC)* 0.000 description 1
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- 125000005981 pentynyl group Chemical group 0.000 description 1
- 239000003209 petroleum derivative Substances 0.000 description 1
- 239000000825 pharmaceutical preparation Substances 0.000 description 1
- LIGACIXOYTUXAW-UHFFFAOYSA-N phenacyl bromide Chemical compound BrCC(=O)C1=CC=CC=C1 LIGACIXOYTUXAW-UHFFFAOYSA-N 0.000 description 1
- 239000002587 phosphodiesterase IV inhibitor Substances 0.000 description 1
- GJQNVZVOTKFLIU-UHFFFAOYSA-N piperidin-1-ium-4-one;chloride Chemical compound Cl.O=C1CCNCC1 GJQNVZVOTKFLIU-UHFFFAOYSA-N 0.000 description 1
- 125000004928 piperidonyl group Chemical group 0.000 description 1
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- 230000004260 plant-type cell wall biogenesis Effects 0.000 description 1
- 201000000317 pneumocystosis Diseases 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
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- 235000019422 polyvinyl alcohol Nutrition 0.000 description 1
- 239000001267 polyvinylpyrrolidone Substances 0.000 description 1
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
- 239000011148 porous material Substances 0.000 description 1
- 239000012254 powdered material Substances 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 229960002429 proline Drugs 0.000 description 1
- OVARTBFNCCXQKS-UHFFFAOYSA-N propan-2-one;hydrate Chemical compound O.CC(C)=O OVARTBFNCCXQKS-UHFFFAOYSA-N 0.000 description 1
- 125000004368 propenyl group Chemical group C(=CC)* 0.000 description 1
- 125000002568 propynyl group Chemical group [*]C#CC([H])([H])[H] 0.000 description 1
- 238000001243 protein synthesis Methods 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 230000004147 pyrimidine metabolism Effects 0.000 description 1
- 150000003230 pyrimidines Chemical class 0.000 description 1
- 125000000719 pyrrolidinyl group Chemical group 0.000 description 1
- 238000010791 quenching Methods 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 125000006413 ring segment Chemical group 0.000 description 1
- 238000005096 rolling process Methods 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
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- 150000004760 silicates Chemical class 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- XGVXKJKTISMIOW-ZDUSSCGKSA-N simurosertib Chemical compound N1N=CC(C=2SC=3C(=O)NC(=NC=3C=2)[C@H]2N3CCC(CC3)C2)=C1C XGVXKJKTISMIOW-ZDUSSCGKSA-N 0.000 description 1
- 229920003109 sodium starch glycolate Polymers 0.000 description 1
- 229940079832 sodium starch glycolate Drugs 0.000 description 1
- 239000008109 sodium starch glycolate Substances 0.000 description 1
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- 239000000829 suppository Substances 0.000 description 1
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- 238000003786 synthesis reaction Methods 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- BWMISRWJRUSYEX-SZKNIZGXSA-N terbinafine hydrochloride Chemical compound Cl.C1=CC=C2C(CN(C\C=C\C#CC(C)(C)C)C)=CC=CC2=C1 BWMISRWJRUSYEX-SZKNIZGXSA-N 0.000 description 1
- 150000003505 terpenes Chemical class 0.000 description 1
- 235000007586 terpenes Nutrition 0.000 description 1
- DPKBAXPHAYBPRL-UHFFFAOYSA-M tetrabutylazanium;iodide Chemical compound [I-].CCCC[N+](CCCC)(CCCC)CCCC DPKBAXPHAYBPRL-UHFFFAOYSA-M 0.000 description 1
- BRNULMACUQOKMR-UHFFFAOYSA-N thiomorpholine Chemical compound C1CSCCN1 BRNULMACUQOKMR-UHFFFAOYSA-N 0.000 description 1
- 125000004568 thiomorpholinyl group Chemical group 0.000 description 1
- 201000004647 tinea pedis Diseases 0.000 description 1
- 201000005882 tinea unguium Diseases 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- CFOAUYCPAUGDFF-UHFFFAOYSA-N tosmic Chemical compound CC1=CC=C(S(=O)(=O)C[N+]#[C-])C=C1 CFOAUYCPAUGDFF-UHFFFAOYSA-N 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
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- 230000014616 translation Effects 0.000 description 1
- 238000002054 transplantation Methods 0.000 description 1
- ILWRPSCZWQJDMK-UHFFFAOYSA-N triethylazanium;chloride Chemical compound Cl.CCN(CC)CC ILWRPSCZWQJDMK-UHFFFAOYSA-N 0.000 description 1
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Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/4353—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom ortho- or peri-condensed with heterocyclic ring systems
- A61K31/437—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom ortho- or peri-condensed with heterocyclic ring systems the heterocyclic ring system containing a five-membered ring having nitrogen as a ring hetero atom, e.g. indolizine, beta-carboline
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P11/00—Drugs for disorders of the respiratory system
- A61P11/06—Antiasthmatics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P15/00—Drugs for genital or sexual disorders; Contraceptives
- A61P15/02—Drugs for genital or sexual disorders; Contraceptives for disorders of the vagina
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P17/00—Drugs for dermatological disorders
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P27/00—Drugs for disorders of the senses
- A61P27/16—Otologicals
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/10—Antimycotics
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P31/00—Antiinfectives, i.e. antibiotics, antiseptics, chemotherapeutics
- A61P31/12—Antivirals
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P37/00—Drugs for immunological or allergic disorders
- A61P37/08—Antiallergic agents
Landscapes
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- Chemical & Material Sciences (AREA)
- Medicinal Chemistry (AREA)
- Pharmacology & Pharmacy (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Pulmonology (AREA)
- Epidemiology (AREA)
- Oncology (AREA)
- Communicable Diseases (AREA)
- Dermatology (AREA)
- Reproductive Health (AREA)
- Endocrinology (AREA)
- Gynecology & Obstetrics (AREA)
- Virology (AREA)
- Immunology (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Applications Claiming Priority (5)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB0510190A GB0510190D0 (en) | 2005-05-18 | 2005-05-18 | Antifungal agents |
| GB0510190.2 | 2005-05-18 | ||
| GB0607841.4 | 2006-04-20 | ||
| GB0607841A GB0607841D0 (en) | 2006-04-20 | 2006-04-20 | Antifungal agents |
| PCT/GB2006/001820 WO2006123145A1 (en) | 2005-05-18 | 2006-05-18 | Antifungal agents |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CA2608977A1 CA2608977A1 (en) | 2006-11-23 |
| CA2608977C true CA2608977C (en) | 2014-09-23 |
Family
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2608977A Active CA2608977C (en) | 2005-05-18 | 2006-05-18 | Antifungal agents |
Country Status (11)
| Country | Link |
|---|---|
| US (1) | US8486962B2 (https=) |
| EP (1) | EP1888063B1 (https=) |
| JP (1) | JP5172661B2 (https=) |
| AT (1) | ATE420639T1 (https=) |
| AU (1) | AU2006248812B2 (https=) |
| CA (1) | CA2608977C (https=) |
| DE (1) | DE602006004865D1 (https=) |
| DK (1) | DK1888063T3 (https=) |
| ES (1) | ES2321230T3 (https=) |
| NZ (1) | NZ563397A (https=) |
| WO (1) | WO2006123145A1 (https=) |
Families Citing this family (23)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB0623209D0 (en) * | 2006-11-21 | 2007-01-03 | F2G Ltd | Antifungal agents |
| GB0710121D0 (en) * | 2007-05-25 | 2007-07-04 | F2G Ltd | Antifungal agents |
| DE102007037579B4 (de) | 2007-08-09 | 2012-05-16 | Emc Microcollections Gmbh | Neue Benzimidazol-2-yl-alkylamine und ihre Anwendung als mikrobizide Wirkstoffe |
| CN101168532B (zh) * | 2007-11-30 | 2010-06-02 | 中科院嘉兴中心应用化学分中心 | 一种n-甲基哌嗪取代苯胺的合成方法 |
| DK2626361T3 (en) | 2008-04-24 | 2015-01-19 | F2G Ltd | Pyrrol-Antimycotics |
| GB0809773D0 (en) * | 2008-05-29 | 2008-07-09 | F2G Ltd | Antifungal combination therapy |
| CN103153958A (zh) | 2010-07-02 | 2013-06-12 | 先正达参股股份有限公司 | 新颖的杀微生物的二肟醚衍生物 |
| CN103038217A (zh) | 2010-07-29 | 2013-04-10 | 先正达参股股份有限公司 | 新颖的杀微生物的二肟醚衍生物 |
| BR112013006671A2 (pt) | 2010-09-23 | 2016-06-07 | Syngenta Participations Ag | microbiocidas21 |
| WO2012062844A1 (en) | 2010-11-12 | 2012-05-18 | Syngenta Participations Ag | Novel microbiocides |
| WO2012117021A2 (en) | 2011-03-03 | 2012-09-07 | Syngenta Participations Ag | Novel microbiocidal oxime ethers |
| UY34279A (es) | 2011-08-23 | 2013-04-05 | Syngenta Participations Ag | Compuestos heterocíclicos activos como microbiocidas, intermediarios, composiciones y usos |
| WO2013092460A1 (en) | 2011-12-20 | 2013-06-27 | Syngenta Participations Ag | Cyclic bisoxime microbicides |
| US20150025105A1 (en) * | 2012-02-09 | 2015-01-22 | Praveen Rao Perampalli Nekkar | Indolizine derivatives |
| EP2641901A1 (en) | 2012-03-22 | 2013-09-25 | Syngenta Participations AG. | Novel microbiocides |
| CN102964256B (zh) * | 2012-11-28 | 2014-05-07 | 浙江海翔药业股份有限公司 | 一种4-氨基-n,n-二甲基苄胺的制备方法 |
| CN104744302A (zh) * | 2013-12-31 | 2015-07-01 | 上海药谷药业有限公司 | 一种2-(4-氨基苯基)-2-甲基丙腈化合物的制备方法 |
| CA2982660C (en) * | 2014-11-21 | 2023-01-24 | F2G Limited | 2-(1,5-dimethyl-3-phenyl-1h-pyrrol-2-yl)-n-(4-(4-(5-fluoropyrimidin-2-yl)piperazine-1-yl)phenyl)-2-oxoacetamide and derivatives thereof for use as antifungal agents |
| GB201609222D0 (en) | 2016-05-25 | 2016-07-06 | F2G Ltd | Pharmaceutical formulation |
| US11819503B2 (en) | 2019-04-23 | 2023-11-21 | F2G Ltd | Method of treating coccidioides infection |
| CN112898316A (zh) * | 2019-12-03 | 2021-06-04 | 微境生物医药科技(上海)有限公司 | 新型吡咯化合物 |
| CN114644634B (zh) * | 2020-12-21 | 2023-06-20 | 深圳市祥根生物医药有限公司 | 一种吡咯衍生物及其制备方法和用途 |
| CN114031502A (zh) * | 2021-10-09 | 2022-02-11 | 南京一苇医药科技有限公司 | 一种对硝基苯丙酮的制备方法 |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BR9508298A (pt) | 1994-07-21 | 1998-11-03 | Shionogi & Co | Inibidores de indolizina de spla2 |
| EP1399442B1 (en) * | 2001-06-06 | 2006-08-09 | Vertex Pharmaceuticals Incorporated | Cak inhibitors and uses thereof |
| CA2517034A1 (en) | 2003-03-13 | 2004-09-30 | Synta Pharmaceuticals Corp. | Fused pyrrole compounds |
-
2006
- 2006-05-18 AT AT06743919T patent/ATE420639T1/de not_active IP Right Cessation
- 2006-05-18 DE DE602006004865T patent/DE602006004865D1/de active Active
- 2006-05-18 EP EP06743919A patent/EP1888063B1/en active Active
- 2006-05-18 CA CA2608977A patent/CA2608977C/en active Active
- 2006-05-18 WO PCT/GB2006/001820 patent/WO2006123145A1/en not_active Ceased
- 2006-05-18 US US11/914,516 patent/US8486962B2/en active Active
- 2006-05-18 AU AU2006248812A patent/AU2006248812B2/en not_active Ceased
- 2006-05-18 DK DK06743919T patent/DK1888063T3/da active
- 2006-05-18 JP JP2008511788A patent/JP5172661B2/ja not_active Expired - Fee Related
- 2006-05-18 ES ES06743919T patent/ES2321230T3/es active Active
- 2006-05-18 NZ NZ563397A patent/NZ563397A/en not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| EP1888063A1 (en) | 2008-02-20 |
| AU2006248812A1 (en) | 2006-11-23 |
| ATE420639T1 (de) | 2009-01-15 |
| US20080161302A1 (en) | 2008-07-03 |
| US8486962B2 (en) | 2013-07-16 |
| EP1888063B1 (en) | 2009-01-14 |
| JP2008545647A (ja) | 2008-12-18 |
| ES2321230T3 (es) | 2009-06-03 |
| NZ563397A (en) | 2010-04-30 |
| DE602006004865D1 (de) | 2009-03-05 |
| CA2608977A1 (en) | 2006-11-23 |
| AU2006248812B2 (en) | 2012-02-16 |
| DK1888063T3 (da) | 2009-05-11 |
| WO2006123145A1 (en) | 2006-11-23 |
| JP5172661B2 (ja) | 2013-03-27 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| EEER | Examination request |